Songfacts®:

• This song tells of an encounter between two high school classmates a decade later. The two friends bring each other up to date and share with each other the hard life lessons they've learnt along the way.
• Pat Monahan trades vocals with the country singer-songwriter Ashley Monroe on this song. The songstress takes the part as a single mom whilst Train's frontman sings of maybe wanting to be more than friends with her after their chance encounter. Monroe is best known for being a member of the all-female trio Pistol Annies as well as co-penning several of Miranda Lambert's cuts.
• The song is Pat Monahan's second hookup with a Nashville female vocalist following their collaboration on Martina McBride's version of "Marry Me."
• The song was re-recorded with French-Canadian singer Marilou in both English and French for its Canadian single release.
• Monahan explained to Radio.com how he teamed up with Ashley Monroe. "Ashley's been a friend of mine for a long time," he explained. "I met her when she was 19. The guy that used to run Columbia Records introduced her to me because she wanted to write with me. When I met her I realized that I was the lucky one to be in the room with her. She's a great writer."
• Monahan told Radio.com the story behind the song. "I wrote the song in New York," he said. "It was just real easy. I run into people I went to high school with and realize how much older we are, and how much more we've been through and a lot of it isn't all that fun and it makes us more beautiful if you can see it that way. That song was really easy to write because it is a very true story and Ashley was the perfect girl to sing on it."